Triethylamine → N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine

HRID 1060676

반응식

HRID 1060676 반응식
[NH2:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5]1.[Cl:17][C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[C:22](Cl)[C:21]([CH3:28])=[C:20]([CH3:29])[N:19]=1.C(N(CC)CC)C>CN(C)C=O>[CH2:10]([N:7]1[CH2:6][CH2:5][CH:4]([CH2:3][CH2:2][NH:1][C:22]2[C:21]([CH3:28])=[C:20]([CH3:29])[N:19]=[C:18]([Cl:17])[C:23]=2[N+:24]([O-:26])=[O:25])[CH2:9][CH2:8]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 18670022-(1-Benzylpiperidin-4-yl)ethan-1-amineHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridine

생성물 1

HCID 21973806N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine수율 60.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 4-(2-aminoethyl)-1-benzylpiperidine (9.88 g, 45.2 mmol) in N,N-dimethylformamide was added dropwise to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (10.00 g, 45.2 mmol) and triethylamine (12.6 mL, 90.5 mmol) in N,N-dimethylformamide (320 mL). The reaction mixture was allowed to stir at ambient temperature for about 20 hours and then it was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organics were combined, washed with brine, dried over sodium sulfate and then concentrated under reduced pressure to provide an orange oil. The oil was purified by flash chromatography (400 mL silica gel eluting initially with 10% ethyl acetate in hexane, then with 15% ethyl acetate in hexane and finally with 40% ethyl acetate in hexane) to provide 11.00 g of N-[2-(1-benzylpiperidin-4-yl)ethyl]-2-chloro-5,6-dimethyl-3-nitropyridin-4-amine.

후처리

  1. concentrationit was concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto provide an orange oil
  9. customThe oil was purified by flash chromatography (400 mL silica gel eluting initially with 10% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-f3c60fd7dc6b4ad6bd7a5ec809c6396d
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525064B1

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